Summary
The reactions of N,N,N′,N′-tetramethylthiuram disulfide (tmtds) with gold(III) complexes of the [Au(L)X3] type [L = N-methylimidazole (N-Melm), 2-methylbenzoxazole (2-MeBO) and 2,5-dimethylbenzoxazole (2,5-diMeBO), X = Cl, Br or I] are reported, and yielded two main types of product - [Au(Me2dtc)X2] (A) and [Au(Me2dtc)2]X (B) (Me2dtc = N,N-dimethyldithiocarbamato anion). The ratio of the product yields (B/A) depends upon the nature of the ligand (L) and halogen (X). The ratio B/A for the reaction: [Au(L)Cl3] + tmtds = A + B, increases in the sequence N-MeIm < 2- MeBO < 2,5-diMeBO, which correlates well with the level of cytotoxic activity exhibited by the [Au(L)Cl3] complexes. A and B were characterized by their i.r., u.v-vis. and 1-n.m.r. spectra. The magnetic measurements were also recorded. The data support a squareplanar geometry for gold(III) complexes with the Me2dtc ligand bonded in a bidentate fashion; a conjecture has been verified crystallographically for [Au(Me2NCS2)2]-Br·2H2O. The X-ray analysis confirmed that the complex is composed of ionic units: [Au(Me2dtc)2] + and Br− and H2O molecules. The Au—S distances are markedly similar, falling in the 2.343(4)–2.350(3) ∘A range.
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References
V. P. Dyadchenko, Usp. Khim., 51, 467 (1982).
K. I. Grandberg, Usp. Khim., 51, 438 (1982).
V. P. Dyadchenko, K. I. Grandberg, O. N. Kalinina, P. E. Krasik, O. Yu Burtseva, M. A. Porai-Koshits, L. G. Kuz'mina and E. G. Perevalova, Metallorg. Khim., 3, 667 (1990).
S. Åkerström, Ark. Kemi, 14, 387 (1959); P. T. Beurskens, J. A. Cras and J. J. Steggerda, Inorg. Chem., 7, 810 (1968).
P. T. Beurskens, J. A. Cras and J. G. M. van der Linden, Inorg. Chem., 9, 475 (1970).
F. Forghieri, C. Preti, L. Tassi and G. Tosi, Polyhedron, 7, 1231 (1988).
J. A. Cras and J. Willemse, Comprehensive Coordination Chemistry, Pergamon Press, Oxford, 1987, Vol. 2, p. 591; and refs cited therein.
J. A. McCleverty and N. J. Morrison, J. Chem. Soc., Dalton Trans., 2169 (1976); J. A. McCleverty, S. Gill, R. S. Z. Kowalski, N. A. Bailey, H. Adams, K. W. Lumbard and M. A. Murphy, J. Chem. Soc., Dalton Trans., 493 (1982).
R. A. Bulman, Struct. Bonding (Berlin), 67, 91 (1987).
M. Massacesi, R. Pinna, G. Ponticelli and G. Puggioni, J. Inorg. Biochem., 29, 95 (1987).
G. Floris, A. Padiglia, G. Ponticelli and G. Puggioni, Transition Met. Chem., 17, 145 (1992).
M. Massacesi, Z. D. Matović and G. Ponticelli, Farmaco, 48, 1327 (1993).
I. A. Efimenko, A. P. Kurbakova, Z. D. Matović and G. Ponticelli, Transition Met. Chem., 19, 539 (1994).
I. A. Efimenko, A. P. Kurbakova, Z. D. Matović and G. Ponticelli, Transition Met. Chem., 19, 640 (1994).
Z. D. Matović, D. J. Radanović, G. Ponticelli, P. Scano and I. A. Efimenko, Transition Met. Chem., 19, 461 (1994).
D. J. Radanović, Z. D. Matović, G. Ponticelli, P. Scano and I. A. Efimenko, Transition Met. Chem., 19, 646 (1994).
F. Cosu, Z. D. Matović, D. J. Radanović and G. Ponticelli, Farmaco, 49, 301 (1994).
G. Ponticelli, F. Cossu and Z. D. Matović, Fourth Int. Symp. Comb. Therapies, Cagliari, Italy, 1994, p. 104.
N. A. Malik, G. Otiko and P. J. Sadler, J. Inorg. Biochem., 12, 317 (1980)
A. A. Isab, A. L. Hormann, D. T. Hill, D. E. Griswold, M. J. DiMartino and C. F. Shaw III, Inorg. Chem., 28, 1321 (1989).
S. Wang and J. P. Fackler Jr, Inorg. Chem., 29, 4404 (1990).
C. F. Shaw III, Inorg. Persp. Biol. Med., 2, 344 (1979).
R. J. Puddephatt, The Chemistry of Gold, Elsevier, New York, 1978
I. Haiduc and C. Silvestru, Coord. Chem. Rev., 99, 253 (1990)
P. J. Sadler, Struct. Bonding (Berlin), 28, 171 (1978).
F. Ugozzoli, Absorb, A Program for Walker and Stuart's Absorption Correction, University of Parma, 1983.
International Tables for X-ray Crystallography, Kynoch Press, Birmingham, UK, 1974, Vol. 4.
G. M. Sheldrick, SHELX86, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1986.
G. M. Sheldrick, SHELX92, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1992.
C. K. Johnson, ORTEP, Rep. ORNL-3794, Oak Ridge, TN, USA, 1965.
M. Nardelli, Comput. Chem., 7, 95 (1983).
F. A. Cotton and J. A. McCleverty, Inorg. Chem.,3, 1398 (1964).
E. W. Ainscough and A. M. Brodie, J. Chem. Soc., Dalton Trans., 565 (1977).
G. V. Boyd, Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1984, Vol. 6, p. 191.
H. J. A. Blaauw, R. J. F. Nivard and G. J. M. van der Kerk, J. Organometal. Chem., 2, 236 (1964).
J. J. Criado, J. A. Lopez-Arias, B. Macias, L. R. Fernandez-Lago and J. M. Salas, Inorg. Chim. Acta, 193, 229 (1992).
P. T. Beurskens, H. J. A. Blaauw, J. A. Cras and J. J. Steggerda, Inorg. Chem., 7, 805 (1968).
D. A. Brown, W. K. Glass and M. A. Burke, Spectrochim. Acta, 32, 137 (1976).
J. R. Ferraro, Low-frequency Vibrations of Inorganic and Coordination Compounds, Plenum Press, New York, 1971.
W. R. Mason and H. B. Gray, J. Am. Chem. Soc., 90, 5721 (1968); W. R. Mason and H. B. Gray, Inorg. Chem., 7, 55 (1968).
J. H. Noordik, Cryst. Struct. Commun., 2, 81 (1973).
M. Hong, Z. Huang, X. Lei, F. Jiang and H. Liu, Acta Crystallogr., Sect. C, 48, 1101 (1992).
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Radanović, D.J., Matović, Z.D., Miletić, V.D. et al. Reaction products distribution between square-planar gold(III) complexes and N,N,N′,N′-tetramethylthiuram disulfide. Crystal structure of bis(N,N-dimethyldithiocarbamato)gold(III) bromide dihydrate, [Au(Me2NCS2)2]Br·2H2O. Transition Met Chem 21, 169–175 (1996). https://doi.org/10.1007/BF00136550
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DOI: https://doi.org/10.1007/BF00136550